1beta,10alpha,4alpha,5beta-diepoxyglechoman-8alpha,12-olide - Compound Card

1beta,10alpha,4alpha,5beta-diepoxyglechoman-8alpha,12-olide

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1beta,10alpha,4alpha,5beta-diepoxyglechoman-8alpha,12-olide

Structure
Zoomed Structure
  • Family: Plantae - Apiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene
Canonical Smiles O=C1O[C@@H]2C(=C1C)CC1O[C@]1(C)CCC1[C@@](C2)(C)O1
InChI InChI=1S/C15H20O4/c1-8-9-6-12-14(2,19-12)5-4-11-15(3,18-11)7-10(9)17-13(8)16/h10-12H,4-7H2,1-3H3/t10-,11?,12?,14+,15-/m0/s1
InChIKey CWAJEURPJYKGRL-QUGNMKPDSA-N
Formula C15H20O4
HBA 4
HBD 0
MW 264.32
Rotatable Bonds 0
TPSA 51.36
LogP 2.12
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 19
Formal Charge 0
Fraction CSP3 0.8
Exact Mass 264.14
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Smyrnium olusatrum Apiaceae Plantae 40962

Showing of synonyms

  • El-Gamal AA (2001). Sesquiterpene lactones from Smyrnium olusatrum. Phytochemistry,2001,57(8),1197-1200. [View]
Pubchem: 162936992

No compound-protein relationship available.

Structure

SMILES: C12C(O2)CCC3C(O3)CC4C(C1)=CC(=O)O4

Level: 0

Mol. Weight: 264.32 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp)
-4.93
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.52
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.14

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.06
Plasma Protein Binding
10.57
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
15.06
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.68
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
-0.3
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.0
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-1.71
Rat (Acute)
1.91
Rat (Chronic Oral)
1.3
Fathead Minnow
4.0
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
332.71
Hydration Free Energy
-5.18
Log(D) at pH=7.4
2.11
Log(P)
1.38
Log S
-2.07
Log(Vapor Pressure)
-3.3
Melting Point
51.23
pKa Acid
5.61
pKa Basic
3.46
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.9000
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.9000
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8124
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8124
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7442
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7442
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7337
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7337
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7310
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7310
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7297
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7297
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7239
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7239
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7177
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7177
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7104
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7104
Jasmonoyl--L-amino acid synthetase JAR1 Q9SKE2 JAR1_ARATH Arabidopsis thaliana 3 0.7090
Jasmonoyl--L-amino acid synthetase JAR1 Q9SKE2 JAR1_ARATH Arabidopsis thaliana 3 0.7090
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7078
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7078
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7036
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7036

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